If I were going back to school this fall, I'd stick to my "I-need-to-be-awake-but-put-together" with a button down and chinos. Something that says to my professor, "I enjoy your lectures and your intelligence—and I would like to meet with you after class...to not talk about class over beers at Shakespeare's."

One of my favorite parts about this unique short-sleeve button down is the middle seam that runs straight through the middle of the garment. Quirky? A little. It's a nice touch in breaking up the shirt, making it subtle and casual.

One of the better-fitting pair of chinos I own is the "Davis" Chino by Club Monaco. Slim cut, medium rise, chino-style pockets. I sized down in these and am surprised at how well they hold their fit and feel. I'm definitely stocking up on them when the new fall colors come out. For me, it fits better than J.Crew's Urban Slim Fit, and I used to swear by those.

On Jeff: White short sleeve buton down by rag & bone; the "Davis" chino by Club Monaco; thrifted Allen Edmonds; ivory straw hat with chambray fabric from Target; camper watch by Timex.

To much ankle. The pants need to be an inch longer so you can cuff 1 inch, and show 1 inch of ankle 2 inches at most. Be thankful we have color, even though you're going for something monochromatic and minimalist, try a dash of color maybe with the shoes or hat or perhaps both. And for that matter try a suede saddle shoe. Great idea though, love the minimalism.